The hydroamination of commodity and specialty alcohols, aldehydes and ketones to manufacture the corresponding aliphatic amines is known in the art. The selection of a catalyst with optimal advantages has also been the focus of much research. Aliphatic amines are of considerable industrial importance and find applications in many facets of modern technology, agriculture and medicine.
For example, U.S. Pat. No. 3,270,059 discloses the production of diaminoalkanes by passing an alkanediol, alkanolamine, alkylene oxide, or alkyleneimine along with either ammonia or an alkylamine in the presence of hydrogen and at an elevated temperature over a catalyst which contains sintered cobalt or nickel.
In an article titled "Equilibrium Conditions for Amination of Alcohols and Carbonyl Compounds", i Ind. Eng. Chem. Prod Res. Develop., 11, 3, 333-337(1972), Josef Pasek, et al. described the influence of pressure, temperature, and initial composition, on the equilibrium content of primary, secondary, and tertiary amines in unsaturated compounds.
Alfons Baiker et al., in an article titled "Catalytic Amination of Long Chain Aliphatic Alcohols", Ind. Eng. Chem., Prod. Res. Dev., 16, 3, 261-266 (1977), discuss the amination of dodecanol with dimethylamine and note a preference for using a copper catalyst.
In Russian Patent No. 798094 (1981) there is disclosed the preparation of primary aliphatic amine compounds by reduction-amination of 4-19 carbon aldehydes using liquid ammonium and hydrogen.
The amination of alcohols, aldehydes, and ketones using catalysts containing nickel, copper, or both, has been also been described, for example, in U.S. Pat. No. 4,153,581 and U.S. Pat. No. 4,152,353 and U.S. Pat. No. 4,409,399. These patents do not appear to contemplate the production of diamines.
French patent FR 2 656 864 describes a two-stage process for preparing aliphatic diamines from the corresponding dialdehydes.
DE-C 824 492 discloses a process for preparing aliphatic diamines having a long chain by introducing the corresponding dialdehyde.
The process disclosed in U.S. Pat. No. 4,683,336 employs a catalyst comprising carbonates of copper, nickel, and cobalt, or mixtures thereof to produce amines from aliphatic alcohols or aliphatic aldehydes.
U.S. Pat. No. 4,806,690 discloses a method of preparing amines from an alcohol, aldehyde, ketone or mixture thereof, in the presence of a catalyst containing about 1 to 20% cobalt, 75 to 95% copper, 1 to 16% of a third component selected from iron, zinc, zirconium, and mixtures thereof. The preferred embodiment demonstrates the reductive amination of MEA.
In an article titled "Ethylenediamine by Low-Pressure Ammonolysis of Monoethanolamine", Ind. Eng. Chem. Prod. Res. Dev., 20, 2, 339-407 (1981), by Charles Barnes et al., there is a detailed study of a catalytic route to ethylenediamine and monoethanolamine.
In an article titled "Shape Selective Mordenite-Catalyzed Amination of Ethanolamine to Ethylenediamine", Journal of Molecular Catalysis, 60, 11-17 (1990), M. E. Ford et al. disclose the use of hydrogen mordenite and dealuminated hydrogen mordenite to catalyze the reaction of ethanolamine with ammonia to form ethylenediamine at low pressure.
In Catalysis of Organic Reactions, Blackburn, D. W., ed., 1990, at Chapter 14, M. Ford et al. review the selective synthesis of mixed alkyl amines by amine-alcohol reactions over hydrogen phosphate.
U.S. Pat. No. 5,055,618 teaches the preparation of an .alpha.,.omega.-diamine from an .alpha..omega.-dialdehyde by a method which allows the reaction to be carried out even at relatively high temperatures. This process makes use of the presence of water in the reaction of the dialdehyde and primary amine.
U.S. Pat. No. 5,475,141 discloses that both monoaldehydes and organic compounds having more than one aldehyde group can be reductively aminated in a single stage, by combining an aldehyde and a diluent, where in the case of an alcohol or water as diluent, the mixture is combined at sufficiently low temperatures for no hemi-or semiacetal or no aldehyde hydrate to be formed in the mixture, and by bringing the mixture practically simultaneously into contact with ammonia, a hydrogenation catalyst and hydrogen.
In an article titled "Selective Synthesis of Ethylenediamine from Ethanolamine Over Modified H-Mordenite Catalyst", 11.sup.th International Congress on Catalysis--40.sup.th Anniversary, Studies in Surface Science and Catalysis, 101, 267, (1996) J. W. Hightower et al. (Eds.) Elsevier Science, K. Segawa et al. disclose that a zeolitic catalyst mordenite, treated with ethylenediamine, displayed high activity and selectivity for the formation of ethyleneamine, with small amounts of ethyleneimine and piperizine side products.
In the foregoing references there does not appear to be a disclosure of the amination of a compound such as a hydroxyaldehyde, to an aliphatic diamine. It would be very desirable in the art if a process were available for aminating a compound containing hydroxy and aldehyde functions which is available in large volumes, such as, for example 3-hydroxypropanal, to form 1,3-diaminopropane. This would provide an attractive route to an added-value commodity chemical. These diamines could find large volume applications in polyamide resins as monomer/comonomers, as well as price-competitive usage in lube oils, epoxies, hot melt adhesives, and surfactants. They might also be useful in fuel additives, chelating agents, fungicides, and plastic lubricants. It would also be very desirable if such a reaction could take place in one step with high selectivity.